Hydrochloric Acid → N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide

HRID 2223109Notes

Reaction equation

HRID 2223109 reaction equation
[Br:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:10]([OH:26])=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1>[C:23]([C:11]1[C:10]([OH:26])=[C:9]([NH:8][C:3](=[O:4])[C:2]([Br:1])([CH3:7])[CH3:6])[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 111060492-Bromo-2-methylpropanoyl chlorideHCID 210728221-(3-Amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone

Product 1

HCID 21072865N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.64 g (25 mmol) of 2-bromo-2-methylpropionyl chloride are added dropwise to a solution of 5.15 g (20 mmol) of 1-(3-amino-5-benzyloxy-2-hydroxyphenyl)ethanone in 20 mL of pyridine at 5° C.-20° C. After the addition has ended, the mixture is stirred for 15 minutes, combined with ice water and 100 mL of ethyl acetate and acidified with concentrated hydrochloric acid. The organic phase is separated off, washed with water, and dried with sodium sulfate. After the solvent has been distilled off, the residue is crystallized from a diethyl ether/petroleum ether mixture. Yield: 6.8 g (84%); melting range: 88° C.-90° C.

Workup

  1. additionAfter the addition
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. distillationAfter the solvent has been distilled off
  6. customthe residue is crystallized from a diethyl ether/petroleum ether mixture

Sources & evidence

ORD record
ord-44a45aa4b5764e45a868d668d0289edd
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

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